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1,1'-Carbonyldiimidazole → Tert-butyl 3-[methoxy(methyl)carbamoyl]pyrrolidine-1-carboxylate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| 反応物 | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| 反応物 | 1-((Tert-butoxy)carbonyl)pyrrolidine-3-carboxylic acid | HCID 2760529 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | Tert-butyl 3-[methoxy(methyl)carbamoyl]pyrrolidine-1-carboxylate | HCID 57419605 | 90% |
反応手順
Add in one portion 1,1′-carbonyldiimidazole (8.3 g, 51 mmol) to a solution of pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (10.0 g, 46.5 mmol) in dichloromethane (155 mL) at RT. Allow the mixture to stir for 15 min. Add slowly N,O-dimethylhydroxylamine hydrochloride (5.4 g, 55.8 mmol). Stir the reaction mixture at RT overnight. Dilute the mixture with dichloromethane (200 mL), wash with water (2×300 mL), brine (200 mL), dry over Na2SO4, filter, and concentrate. Purify the crude material by flash chromatograph and elute with 50-100% ethylacetate/hexane to give 10.8 g (90%) of the title compound. LC-MS/ES m/z 203.0 [M-tert-Bu+H]+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08101764B2 |
| 出典データセット | uspto-grants-2012_01 |
| ORD ID | ord-5a2427e5e4d943378acb9ddb6e26de1e |
| 出典メモ | uspto-grants-2012_01 |